O-alpha-methyl mandelate-N-trimethyl chitosan quaternary ammonium salt as well as preparation method and application thereof

A technology of trimethyl chitosan and methyl mandelate, applied in the direction of antibacterial drugs, etc., can solve problems such as insolubility in water, and achieve enhanced antibacterial activity and hydrophilicity, good antibacterial properties, and expanded application scope. Effect

Inactive Publication Date: 2017-02-08
HUNAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to overcome the shortcoming that chitosan macromolecules are insoluble in water, the primary purpose of the present invention is to prov

Method used

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  • O-alpha-methyl mandelate-N-trimethyl chitosan quaternary ammonium salt as well as preparation method and application thereof
  • O-alpha-methyl mandelate-N-trimethyl chitosan quaternary ammonium salt as well as preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0029] A kind of O-alpha-methyl mandelic acid ester-N-trimethyl chitosan quaternary ammonium salt, its preparation method is as follows:

[0030] (1) Dissolve 2g of chitosan in 100mL of 15% formic acid solution, stir and heat up to 50 oC , add 6mL of formaldehyde solution, mix evenly and transfer to a microwave normal pressure reactor, adjust the microwave power to 200W, temperature 50 oC React for 40 minutes; adjust pH to alkaline with 10% NaOH solution, filter with suction, wash with water until neutral, add to 50mL N-methyl-2-pyrrolidone after drying, add 6mL methyl iodide, 50 oC React for 120 hours; add twice the volume of V (ether) / V (ethanol) = 1:1 mixed solvent for precipitation, use deionized water to dialyze and freeze-dry to obtain N,N,N-trimethyl chitosan.

[0031] The sample was detected by X-ray photoelectron spectroscopy (XPS), and the N-position quaternization substitution degree of N,N,N-trimethyl chitosan was measured to be 76%.

[0032] (2) Weigh 1g of N,N,...

Embodiment 2

[0035] A kind of O-alpha-methyl mandelic acid ester-N-trimethyl chitosan quaternary ammonium salt, its preparation method is as follows:

[0036] (1) Dissolve 2g of chitosan in 100mL of 15% formic acid solution, stir and heat up to 50 oC , add 6mL of formaldehyde solution, mix evenly and transfer to microwave normal pressure reactor, adjust microwave power to 400W, temperature 60 oCReact for 30 minutes; use 10% NaOH solution to adjust the pH to alkaline, filter with suction, wash with water until neutral, add to 50mL N-methyl-2-pyrrolidone after drying, add 12mL methyl iodide, 60 oC React for 80 minutes; add twice the volume of V (ether) / V (ethanol) = 1:1 mixed solvent for precipitation, use deionized water to dialyze and freeze-dry to obtain N,N,N-trimethyl chitosan.

[0037] The sample was detected by X-ray photoelectron spectroscopy (XPS), and the N-position quaternization substitution degree of N,N,N-trimethyl chitosan was measured to be 79%.

[0038] (2) Weigh 1g of N,N...

Embodiment 3

[0041] A kind of O-alpha-methyl mandelic acid ester-N-trimethyl chitosan quaternary ammonium salt, its preparation method is as follows:

[0042] ((1) Dissolve 2g of chitosan in 100mL of 15% formic acid solution, stir and heat up to 50 oC , add 6mL of formaldehyde solution, mix evenly and transfer to microwave normal pressure reactor, adjust microwave power to 600W, temperature 70 oC React for 20 minutes; use 10% NaOH solution to adjust the pH to alkaline, filter with suction, wash with water until neutral, add to 50mL N-methyl-2-pyrrolidone after drying, add 18mL methyl iodide, 70 oC React for 40 minutes; add twice the volume of V (ether) / V (ethanol) = 1:1 mixed solvent for precipitation, use deionized water to dialyze and freeze-dry to obtain N,N,N-trimethyl chitosan.

[0043] The sample was detected by X-ray photoelectron spectroscopy (XPS), and the N-position quaternization substitution degree of N,N,N-trimethyl chitosan was measured to be 85%.

[0044] (2) Weigh 1g of N...

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Abstract

The invention belongs to the field of high molecular compound materials and discloses a chitosan-chemically modified functional derivative, namely O-alpha-methyl mandelate-N-trimethyl chitosan quaternary ammonium salt as well as a preparation method and application thereof. The preparation method of the O-alpha-methyl mandelate-N-trimethyl chitosan quaternary ammonium salt comprises the following steps: taking chitosan, formaldehyde and formic acid as starting materials, carrying out microwave reaction to obtain chitosan schiff base, and then carrying out reaction with iodomethane to obtain N,N,N-trimethyl chitosan; and dissolving N,N,N-trimethyl chitosan with methane sulfonic acid, and then adding O-alpha-formyl mandelate acyl chloride into the mixed solution for reacting so as to obtain the O-alpha-methyl mandelate-N-trimethyl chitosan quaternary ammonium salt. The O-alpha-methyl mandelate-N-trimethyl chitosan quaternary ammonium salt has good water solubility, has greatly increased antibacterial properties compared with the chitosan raw material and N,N,N-trimethyl chitosan, and can be applied to many application fields of antibacterial medical materials, chemical products for daily use, food packages and the like.

Description

technical field [0001] The invention belongs to the field of polymer compound materials, and in particular relates to a functional derivative O-α-methylmandelate-N-trimethyl chitosan quaternary ammonium salt chemically modified by chitosan and its preparation method and application . Background technique [0002] With the rapid development of science and technology and the steady improvement of people's living standards, the public pays more and more attention to packaging materials with antibacterial properties. Currently. There are three main types of antibacterial agents commonly used in daily life: inorganic metal mineral materials, organic heterocyclic antibacterial materials and natural antibacterial materials. Because natural antibacterial materials come from nature, are highly safe to the human body, and meet the requirements of green environmental protection, they have been widely welcomed by people in recent years. Therefore, the research, development and utiliz...

Claims

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Application Information

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IPC IPC(8): C08B37/08A61K31/722A61P31/04
CPCC08B37/003A61K31/722
Inventor 李知函钟泽辉刘跃军
Owner HUNAN UNIV OF TECH
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